The Daedric Wager
A Skyrim Fanfiction

Riaien sighed and brushed a lock of dark hair behind one ear. "Quite the incoming problem we have on our hands..." They were away from Dragon's Reach and the Cloud District now, but she was still mindful of the volume of her voice as they headed for the main gates and the stables beyond. She huffed unhappily. "Some invitation. They might as well be holding daggers to our throats."

"It can't be helped," Karliah said alongside her, resigned more than anything. "Something like this was bound to happen eventually, with the way things have been going. We've gotten through worse. It won't be the end of us."

The short, black-clad assassin laughed darkly somewhere a few steps ahead of them, walking faster than anyone as if he couldn't wait to put the city to his back. Riaien already sensed incoming cynicism.

"You should learn from the Brotherhood's mistakes," he sneered, tilting his head back over his shoulder slightly. "The last time they struck a `deal` with any kind of guild, it was almost at the cost of every life within it."

Riaien could definitely sympathize with the boy's reasoning for resentment. Still, the foul attitude looked to her more like a permanent state of personality, rather than solely a bitter hatred towards only the Legion. Maybe she was wrong on that, but she doubted that to be the case.

"I'm not very fond of these developments either," Irilwe agreed with a deep-set frown. Riaien could understand why, even if the Elf hadn't voiced her reasons already. The College was a place of learning, not a place of war.

It made sense for them to insist on help from the Thieves, Brotherhood, and Companions.

The Thieves were located in Riften, which was Stormcloak territory - if the Stormcloaks had them on their side, they only further held their presence there, but if the Legion gained allyship with the Thieves, they had allies behind enemy lines, which meant they could more easily reclaim that territory, even if only through passed on information and stolen reports.

The Brotherhood was on obvious one. They could send assassins over to take out military officers, perhaps even Ulfric himself, to turn the tides of the war, and from what she knew of them, the Brotherhood's home was nearly impenetrable to launch a proper attack if the Stormcloak's learned of their involvement, or vica versa.

And as for the Companions, it would give either side a chance to take Whiterun, rather than let it remain entirely neutral n the conflict. They would have an excuse to have a presence there, even if they couldn't get the warrior guild to agree to fight their battles.

All of those guilds had great advantages, not only with bolstering numbers, but tactically as well.

The College? The only use would be to have mages on their side, but likely few of them would be interested in fighting. The Legion might like it simply to have territory a little closer to Windhelm, but that was about the only other possible reason, and it wasn't a very good one. Winterhold was too remote and run-down to be of any real tactical use, unless they really wanted to brave the harshest environment rebuilding it with buildings and walls around the place, which would take too long to be of much benefit anyway.

"Likely neither of the groups will have much use for the College," Riaien offered, hoping to be reassuring. "You might take their offer only to keep them placated?"

Irilwe scoffed. "If I take the offer from one side, the other will attack us, and if I agree, they will expect us to fight." She did have a good point. "I've already made my decision."

But could they withstand a siege from both sides? Riaien wondered about that.

"And what of you?" Astasl questioned, having followed them despite that she and her companions very well could have gone back to Jorrvaskr. Riaien suspected - from the looks the Orc was casting towards the black-clad assassin boy - that it was because they wanted to make sure the other groups left. Perhaps the Brotherhood more than anyone else.

Riaien shrugged. "It depends on what the rest of the guild decides on. It would make the most sense, location-wise, for us to take up the Stormcloak's offer, if we take a side at all, but it depends on what benefit both sides would give us and which offers more." The Thieves were, after all, a group that was about profit first and foremost.

"All the same, we'd like to remain uninvolved," Karliah added. "But I fear trying to do so will have both coming to our doorstep armed for war against us as well."

"Aye," Brynjolf agreed. "They're not likely to simply let us off the hook. Just as the Arch-mage said though, if we join one side, the other will target us more than ever, and chances are they won't let us remain idle to their cause when we join one side or the other. On the plus side, since both of their presences were here and made themselves felt, we can probably negotiate both sides until we get the best deal of them possible."

"That's true..." Riaien agreed. She didn't foresee the Thieves not taking a side, it was simply a matter of getting the best spoils out of choosing an alliance, and since both sides seemed so worried to lose to the other, that gave them a lot of leverage. If they played the game especially smart, they could even walk away with the prizes and avoid the fighting. After all, they were still thieves.

"So what of the Companions and the Brotherhood? What are your takes on this?" Brynjolf wondered as they arrived at the stables.

"That all depends," Nazir hummed. "If the pay is good, then we'll do the jobs they ask, but it has to be worth our whiles."

Similar boat as the Thieves, then. Riaien hadn't expected much else, though.

"Of course, whether or not we actually pick sides... that's another matter."

"If we pick sides, it certainly as Oblivion won't be with the Legion," the other assassin hissed, facing elsewhere.

"You don't get to decide that," Nazir admonished.

"Then leave me out of it," they snapped in response. "The only business I want with the Legion is removing their heads from their shoulders. Anyone who hates them and hates the Forsworn is a lot more worth doing a job for in my book."

Divided loyalties? That could be a problem. She knew first-hand already exactly what kind of damage something like divided loyalties and treachery could do. She wondered if she should discuss it, either with Brynjolf and Karliah or even with Nazir himself.

Still, she didn't think she would need to. The Redguard looked like he knew that fact all too well with the look of exasperation and waning patience on his face. For some reason the smaller assassin seemed vaguely familiar, but she supposed that could merely be because the Brotherhood and Thieves did some collaboration work, and the Thieves often procured goods for the Brotherhood when enough coin was involved. It might have only been passing glances.

"Careful, Lad," Brynjolf warned. Riaien couldn't help but think that the tone sounded far too familiar speaking to him. "Making haste judgments like that never ends well."

"Shove your advice," the kid snarled, briefly turning his pale face and showing a snarl, along with a large scar from brow-to-jaw on the left side, though the blue eye on that side was still in-tact. "Nobody asked for it." With that, he whirled and walked off at a rushed pace, black cloak furling behind him.

Nazir sighed audibly. "Regardless of his opinions, he doesn't speak for the rest of the guild. We'll consider what's best for our future and adjust accordingly until this war of theirs blows over one way or another."

It seemed a logical - and thankfully much more level-headed - approach.

"And the Companions?" It was Irilwe this time.

Astasl waved them off. "We have no interest in this fight, but if we must, we may. There has been little for us to do as of late. It may be good for us."

Leave it to a hot-blooded warrior group to be so flippant about their reasons to go to war.

"But to which side?"

"Ysgrimmer and the Companions fought for this land for Nords. It would make sense for us to fight for Stormcloak," she said, before tilting her head to the side as if considering the other side of things. "Though Companions are not all Nord. Many shield-brothers and sisters are of other men and mer. We will only fight for Stormcloak if they are welcome as well. We will discuss and see. Companions fight together or not at all."

So the Companions and Thieves are most likely to side with the Stormcloaks. The Brotherhood is undecided... they might even play both sides at the same time. The College is likely to choose neutrality. I suppose it could be worse than this. We could end up divided to both sides, fighting each other.

"I believe that it would be a good idea for us to all discuss with our guilds what we wish to do," Nazir proposed. "Since this concerns both our own futures, as well as whether or not we may or may not have to fight each other, it would probably be in our best interests to meet again before casting our final decision to the Legion or Stormcloaks. I suspect none of us want to end up fighting each other any more than we want to be fighting soldiers."

"That seems an acceptable plan," Irilwe agreed, approving.

Riaien nodded as well. It was a wise decision on Nazir's part, and she saw no disagreement between any of the other guild leaders.

"Where should the place of meeting be?" Karliah inquired. Everyone looked around in indecision, unsure if they should propose the location or let someone else decide.

"Location-wise, probably somewhere either in the Pale or Eastmarch would be best, assuming we want to make travel distance fairly equal for all parties," Nazir suggested. "The Thieves would have to travel the farthest... but what would you all say to Nightgate Inn, at the foot of Mount Anthor between Whiterun and Windhelm?"

They all considered that, some longer than others, before agreeing. It was a neutral enough location, and isolated enough that there wasn't likely to be either Stormcloaks or Legion there to influence their decisions.

"A week from now?" Brynjolf suggested. That would give them time to travel back, discuss and decide, and meet back again. Then they would have another week to either accept or deny alliance with either side.

"Then we're agreed," Nazir announced. "Until then, take care of yourselves."

With that, they turned and left, following the main road. The Thieves took their own horses east, while Nazir and the mages took a carriage heading north towards the Pale and Winterhold.

"Brynjolf."

"Hm?" The red-haired Nord turned his head towards Riaien.

"That smaller assassin seemed familiar. Who was he?"

"Ah, him," Brynjolf nodded. "He was part of the Thieves for a couple of years. Astrid brought him to us - said she wanted him trained proper in the stealth arts before she put him up to the Brotherhood's kind of business since he was so young at the time."

"Really? I hardly remember him..." Maybe the scar - it had looked like a burn - was new. She didn't think she'd forget a feature like that.

"No surprise. He never was the sociable type, even by the Thieves' standards. In fact he was quiet and skittish as a temple mouse."

"I find that hard to believe..." Riaien couldn't help but muse.

"Believe it or otherwise, it was true. Of course, its been a number of years since then. He was around both when you and Darinel were a part of our group, and left us while Mercer Frey was still among our number, before we figured out what he was really like. People do change in that many number of years. Either way, he was good at it. I mean, really good. Almost born for the role, it seemed, but his loyalties were never to the guild. Its a shame he left us for the Brotherhood, but there was nothing to be done for it except to let him go."

Riaien hummed at that, switching topics as they ascended into the hillscape just below the Throat of the World, so they could dodge the Valthiem towers and Eastmarch to save time reaching Riften. "So what about what we're going to do, about this alliance thing? Same plan as you announced back in Whiterun?"

"Aye, most likely," Brynjolf nodded. "Unless you have other ideas you'd like to share?"

"Not at the moment, no..." Riaien admitted. "If it brings us greater wealth, it might be worth our while. Still, we're not a fighting faction. Espionage, maybe, but that will only manage to earn us further enemies we don't need."

"And there is also the matter of Maven," Karliah added. "If we take the Stormcloak's side, I suspect she won't be terribly happy, since she has connections to the Thalmor and attends their parties near Solitude. She may even see us destroyed, or at the very least, cut off ties. All the same, if we take the Legion's side, the Stormcloaks are bound to make a problem for us to ensure the Rift stays in their control."

"And if we remain neutral, both sides will come after us," Riaien lamented.

"I don't think Maven will entirely disagree with playing both sides to our advantage," Brynjolf speculated. "At the same time, it could bring her trouble she doesn't want as well. Any way you look at it, its going to cause us problems. Big problems. We don't have the man-power to fight a full war, even in self-defense."

"I think that's what they're counting on with all of the guilds," Karliah agreed. "None of us want a fight in the first place, and it will be to our great disadvantage if we have to fight one anyway by being disagreeable."

"So no matter how we slice it, we're fucked," Riaien stated bluntly. She wondered if the other guilds were having their own same discussion right now. They couldn't possibly stand up to an entire army on their own, and it was beginning to look like they would be facing one no matter what they chose, because of a war none of them cared to agree with. Even the Companions - who were formed and maintained because of similar ideals to the Stormcloaks that Skyrim was the rightful home of the Nords - didn't full-heartedly agree with them.

Even with as many new members as we've gained, we don't stand a chance by ourselves, and the Stormcloaks or Legion might just treat us like fodder to be expended. Have us do their fighting and dirty work, then swoop in for victory when we've made the sacrifices. She wasn't so dull as to not have considered that an option already. She didn't think her company or any of the other guilds had missed that possibility either, at least not the ones in charge. They know they could overtake us if they wanted, and they'd probably wipe us all out just to be sure their enemies can't have us. So what do we do?

She pondered the possibilities and outcomes for a long time. Everything from picking a side to playing both sides to fleeing somewhere else, anything to avoid the backlash of this war and their petty feuds and alliances.

Suddenly it hit her, and she couldn't believe she hadn't thought of another possibility before all of the other guilds had separated and gone on their way home. It was a gamble, and she didn't know if the other groups would be on-board for it, but she thought it was a fair assumption to make that they would all like it more than their current declared options.

"As a matter of fact, Brynjolf, I think I've come up with a much better solution for everyone to consider."